I have a lot of feelings on oftnws but one thing that I will always enjoy about it is how intrinsically linked hiccup’s quest for understanding jack as a person is with his understanding of jack’s flight. the first time hiccup witnesses it, Jack is quite literally doing a leap of faith. He is attempting to find himself in this new environment, in this new human body. He instinctively and desperately reaches for the familiar, so he jumps off a cliff in a last ditch effort to find that familiarity. hiccup mistakes this for a suicide attempt, obviously, and doesn’t quite believe jack when he’s told that it isn’t. He doesn’t understand that it is not despair, but joy, that Jack feels when he’s flying, until he brings Jack in flight on toothless. Jack jumping off of toothless’ back, and finally, for perhaps just one moment, finding his center again. The joy and whimsy and fun that defines Jack and his identity makes arguably its first appearance, as he tips his head back and laughs. But hiccup does not truly understand the significance of it, the way it’s tied to who Jack is, the fact that his initial dive off a cliff was a bid for self-actualization, a desperate grab for familiarity, until he himself takes to the skies on the wind’s back. Truly a glorious example of the rule of threes in character work